Tetrabutylammonium Fluoride → HCID 57776239, compound

HRID 251627Notes

Reaction equation

HRID 251627 reaction equation
C([Si](C)(C)[O:6][C:7]([CH3:41])([CH3:40])[CH2:8][CH2:9][C:10]1[CH:15]=[C:14]([C:16]2[C:21]([CH2:22][CH3:23])=[CH:20][CH:19]=[CH:18][C:17]=2[CH2:24][CH3:25])[N:13]=[C:12]([CH3:26])[C:11]=1[CH2:27][N:28]([CH3:39])[C@@H:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:32][CH2:31][CH2:30]1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH2:24]([C:17]1[CH:18]=[CH:19][CH:20]=[C:21]([CH2:22][CH3:23])[C:16]=1[C:14]1[N:13]=[C:12]([CH3:26])[C:11]([CH2:27][N:28]([CH3:39])[C@@H:29]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH2:32][CH2:31][CH2:30]2)=[C:10]([CH2:9][CH2:8][C:7]([CH3:40])([OH:6])[CH3:41])[CH:15]=1)[CH3:25]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66993587HCID 66993587, compound

Product 1

HCID 57776239HCID 57776239, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (S)-[4-[3-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-butyl]-6-(2,6-diethyl-phenyl)-2-methyl-pyridin-3-ylmethyl]-methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amine (120 mg, 0.20 mmol) in THF (8 mL) is treated with tetrabutylammonium fluoride (1.6 mL of 1M solution in THF, 1.6 mmol) at 0° C. The mixture is stirred for 24 hours at room temperature. Aqueous work-up followed by purification by PTLC yields (S)-4-(6-(2,6-Diethyl-phenyl)-2-methyl-3-{[methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amino]-methyl}-pyridin-4-yl)-2-methyl-butan-2-ol as a colorless oil. 1H NMR (CDCl3) 7.65-7.62 (m, 1H), 7.26 (dd, 1H), 7.18-7.06 (m, 5H), 6.96 (s, 1H), 4.02-3.97 (m, 1H), 3.88 (s, 2H), 2.99-2.93 (m, 2H), 2.84-2.2.72 (m, 2H), 2.74 (s, 3H), 2.53 (br s, 1H), 2.39-2.31 (m, 4H), 2.14-2.1.95 (m, 2H), 2.08 (s, 3H), 1.92-1.73 (m, 4H, 1.30 (s, 6H), 1.05 (t, 6H).

Workup

  1. customAqueous work-up followed by purification by PTLC

Sources & evidence

ORD record
ord-93396ba3f2474bc199202392b5cde76f
Source dataset
uspto-grants-2011_01
Patent number
US07863454B2

Reaction notes

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